Phosphorus oxychloride → Ethyl 5-Hydroxy-4-Methyl-7-(3-Methyl-2-Octyl)-Coumarin-3-Propionate

HRID 1112114Notes

Reaction equation

HRID 1112114 reaction equation
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:3]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([CH:11]=1)[OH:10])[CH3:4].[C:18]([CH:21]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:22](OCC)=[O:23])(=O)[CH3:19].P(Cl)(Cl)(Cl)=O>>[OH:10][C:9]1[CH:11]=[C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])[CH:6]=[C:7]2[C:8]=1[C:18]([CH3:19])=[C:21]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:22](=[O:23])[O:12]2

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 73915Diethyl 2-acetylglutarateHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diol

Product 1

HCID 22765004Ethyl 5-Hydroxy-4-Methyl-7-(3-Methyl-2-Octyl)-Coumarin-3-Propionate

Procedure

A mixture of 262 g. (1.109 mole) of 5-(3-methyl-2-octyl)resorcinol, 283 g. (1.23 mole) of diethyl α-acetylglutarate, and 170 g. (1.11 mole) of phosphorus oxychloride protected from atmospheric moisture is stirred at room temperature for 12 days. The mixture is taken up in benzene-ether and the solution is washed several times with water, aqueous sodium bicarbonate, water and dried over anhydrous magnesium sulfate. After removal of the solvent, 441 g. of an oil is obtained, which solidifies on standing.

Workup

  1. additionA mixture of 262 g
  2. washthe solution is washed several times with water, aqueous sodium bicarbonate, water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent, 441 g
  5. customof an oil is obtained

Sources & evidence

ORD record
ord-5cd16492be3548a8a610fa0336f0d8bd
Source dataset
uspto-grants-1978_10
Patent number
US04120873

Reaction notes

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